Dihydrofurochromones from Prionosciadium thapsoides.
Chemical investigations of Prionosciadium thapsoides roots led to the isolation of the new dihydrofurochromones (S)-(+)-4'-O-angeloyl-5-O-methylvisamminol (1) and (S)-(+)-4'-O-senecioyl-5-O-methylvisamminol (2), together with the known coumarins jatamansin, buchtormin, isopteryxin, isosamidin, psoralen, and bergapten. The structures of 1 and 2 were determined by 1D and 2D NMR experiments, and their absolute configuration was established by chemical correlation with (+)-5-O-methylvisamminol (3), whose structure was secured by single-crystal X-ray diffraction analysis and its absolute configuration was established as S by vibrational circular dichroism spectroscopy in comparison to DFT B3LYP/DGDZVP calculations.
Torres-Valencia
J Martín
JM
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, km. 4.5 Carretera Pachuca-Tulancingo, Ciudad Universitaria, Pachuca, Hidalgo, 42076 Mexico. jmartin@uaeh.edu.mx
Chávez-Ríos
O Esther
OE
Cerda-García-Rojas
Carlos M
CM
Burgueño-Tapia
Eleuterio
E
Joseph-Nathan
Pedro
P
D019661:Apiaceae / Q000737:chemistry*; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008800:Mexico; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
C568006:(S)-(+)-4'-O-angeloyl-5-O-methylvisamminol; C568007:(S)-(+)-4'-O-senecioyl-5-O-methylvisamminol; D002867:Chromones